Tautomers and UV-Induced Photoisomerization of a Strongly Intramolecularly H-Bonded Aromatic Azo-Dye: 1-(Cyclopropyl)diazo-2-naphthol


Duarte L., Giuliano B. M., Reva I., Fausto R.

JOURNAL OF PHYSICAL CHEMISTRY A, cilt.117, sa.41, ss.10671-10680, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 117 Sayı: 41
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1021/jp405061b
  • Dergi Adı: JOURNAL OF PHYSICAL CHEMISTRY A
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.10671-10680
  • İstanbul Kültür Üniversitesi Adresli: Evet

Özet

Aromatic azo compounds have a wide range of industrial applications as dyes in optical and color-changing materials and can also be exploited in the design of new photodynamic molecular systems. The azo derivative 1-(cyclopropyl)diazo-2-naphthol was isolated in low-temperature cryogenic matrices, and its molecular structure, tautomeric equilibrium, and photochemical transformations were characterized by infrared spectroscopy and theoretical calculations. Only azo enol forms having the OH group involved in a strong intramolecular hydrogen bond, forming a six-membered ring with the azo group, were found experimentally. Irradiation with a narrowband source in the near-UV range generates different rotameric and tautomeric azo-enol and keto-hydrazone forms that can be interconverted at different irradiation wavelengths.